EP0982313B1 - Fragrance releasing olefinic silanes - Google Patents

Fragrance releasing olefinic silanes Download PDF

Info

Publication number
EP0982313B1
EP0982313B1 EP99306790A EP99306790A EP0982313B1 EP 0982313 B1 EP0982313 B1 EP 0982313B1 EP 99306790 A EP99306790 A EP 99306790A EP 99306790 A EP99306790 A EP 99306790A EP 0982313 B1 EP0982313 B1 EP 0982313B1
Authority
EP
European Patent Office
Prior art keywords
alcohol
cis
trans
salicylate
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP99306790A
Other languages
German (de)
French (fr)
Other versions
EP0982313A3 (en
EP0982313A2 (en
Inventor
Robert James Perry
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
General Electric Co
Original Assignee
General Electric Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by General Electric Co filed Critical General Electric Co
Publication of EP0982313A2 publication Critical patent/EP0982313A2/en
Publication of EP0982313A3 publication Critical patent/EP0982313A3/en
Application granted granted Critical
Publication of EP0982313B1 publication Critical patent/EP0982313B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • the present invention relates to silanes that contain a terminal olefinic moiety and one or more substituent groups derived from fragrant compounds wherein the fragrant compound is regenerated and released by a hydrolysis reaction.
  • the slow sustained release of a fragrant molecule is a highly desirable trait in many personal care products.
  • a number of means have been proposed and implemented to achieve this goal. Among these means are dissolving or suspending fragrant compounds in personal care emulsions (U.S. patents 5,525,588; 5,525,555; 5,490,982; and 5,372,806), encapsulation of a fragrant compound (U.S. patents 5,500,223; 5,324,444; 5,185,155; 5,176,903; and 5,130,171), dissolving a fragrant compound into a hydrophobic phase such as a silicone (U.S.
  • GB-A-2041964 discloses soap compositions and GB-A-2042890 discloses antiperspirant and/or deodorant compositions which contain as a fragrance imparting component at least one silicon compound having attached to silicon at least one group of the general formula - OR wherein R represents the residue remaining after removal of the hydroxyl group from an alcohol selected from cyclic and acylic monoterpene alcohols, essential aryl-substituted aliphatic alcohols and essential aliphatic-substituted phenols.
  • the present invention provides for a silicon compound having the formula: (R 1 O) a (R 2 O) b (R 3 O) c (R 4 ) d (R 5 ) e SiR 6
  • R 1 , R 2 and R 3 are derived from the group of fragrant alcohols consisting of R 1 OH, R 2 OH and R 3 OH as defined in claim 1 with R 4 and R 5 selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms
  • the invention also relates to compositions containing the above silicon compounds.
  • the compounds of the present invention introduce fragrant moieties into an olefinic silane molecule.
  • the olefinic silane molecule is capable of further reaction under hydrosilylation conditions to form a variety of siloxanes that also possess fragrant moieties.
  • These siloxane molecules are useful in a variety of personal care compositions.
  • the present invention is directed to new compositions of matter that are silanes that release a fragrant alcohol, ester, ketone or aldehyde upon particular subsequent chemical reactions. Typically the subsequent chemical reaction that releases the fragrant alcohol is a hydrolysis reaction.
  • these silanes may be reacted to form siloxanes that release a fragrant alcohol upon the same particular subsequent chemical reactions wherein the olefinic silane precursor also releases a fragrant alcohol, ester, ketone or aldehyde.
  • R 1 O a (R 2 O) b (R 3 O) c (R 4 ) d (R 5 ) e SiR 6
  • R 1 , R 2 and R 3 are selected (or
  • olefinic halosilanes or olefinic silicon alkoxides may be employed as starting materials to produce the fragrance-releasing silanes of the present invention.
  • Applicant herewith defines the phrase olefinic silicon alkoxide to be a monomeric silicon compound wherein a single silicon atom is substituted with four monovalent organic substituents one of which is an olefin and one of which is an alkoxide.
  • reaction scheme IV 3-methyl-5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol will react with chloromethylvinylsilane in a similar fashion, reaction scheme IV: as will allyldimethylchlorosilane react with citronellol in a similar, reaction scheme V:
  • the fragrant alcohols that are precursors of the silanes of the present invention are selected from the group consisting of 3-methyl-5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methylbutanol, 3-pentanol, n-pentanol, 2-pentanol, n-hexanol, 2-methylpentanol, 1-decanol, sandela, nonadyl, dimetol, thymol, 1-heptanol, menthol, eugenol, vanillan, o-vanillan, 4-( p -hydroxyphenyl)-2-butanone, syringealdehyde, prenol, cis -3-hexenol, trans-3-hexenol, cis -4-heptenol, trans -2-octenol, trans- 2- cis -6-nonadienol, gerani
  • the fragrance releasing compounds of the present invention are particularly suited to incorporation into personal care products to impart a desirable long lasting fragrance to the products.
  • Suitable uses include but are not limited to deodorants, antiperspirants, skin creams, facial creams, hair care products such as shampoos, mousses, styling gels, protective creams, shaving creams, after shave, cologne, perfume, color cosmetics such as lipsticks, foundations, blushes, makeup, and mascara; and other cosmetic formulations where other silicon containing components have been added and where it is desirable to impart a fragrance.
  • Incorporation of small amounts of the compositions of the present invention into fragrance products such as shaving lotions, colognes, toilet water, and perfumes can impart a desirable long lasting fragrance to these products.
  • silanes of the present invention may incorporated into other products where it is desirable to mask unpleasant odors with a pleasant fragrance for example household cleaning products such as waxes and polishes, automobile cleaning products such as waxes and polishes, detergents, textile coatings, paints, varnishes and the like subject to the limitation that the silane of the present invention be compatible or capable of being rendered compatible with the product in which it is incorporated.
  • Dimethylvinylphenethyloxysilane (150 mL, 1.099 moles) was added to a stirred solution of phenethyl alcohol (124.5 mL, 1.042 moles), triethylamine (TEA, 155 mL, 1.112 moles) and toluene (300 mL) over 1.5 h.
  • reaction was heated to 65°C for 0.5 h then cooled to room temperature, filtered, the filter cake washed with toluene (200 mL), the filtrate concentrated in vacuo and then vacuum distilled (81-85°C/533 Pa (4 mm Hg)) to give product (180.5g, 84%).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Description

  • The present invention relates to silanes that contain a terminal olefinic moiety and one or more substituent groups derived from fragrant compounds wherein the fragrant compound is regenerated and released by a hydrolysis reaction.
    • BACKGROUND OF THE INVENTION
  • The slow sustained release of a fragrant molecule is a highly desirable trait in many personal care products. A number of means have been proposed and implemented to achieve this goal. Among these means are dissolving or suspending fragrant compounds in personal care emulsions (U.S. patents 5,525,588; 5,525,555; 5,490,982; and 5,372,806), encapsulation of a fragrant compound (U.S. patents 5,500,223; 5,324,444; 5,185,155; 5,176,903; and 5,130,171), dissolving a fragrant compound into a hydrophobic phase such as a silicone (U.S. patents 5,449,512; 5,160,494 and 5,234,689), incorporation of a fragrant compound into cross-linked polymers (U.S. patents 5,387,622 and 5,387,411), incorporation of fragrant compounds into permeable laminates (U.S. patents 5,071,704, and 5,008,115), incorporation of fragrant compounds into matrices that soften at body temperature (U.S. patent 4,908,208), incorporation of fragrant compounds into rate controlling membranes (U.S. patent 4,445,641) and derivatization of silanes with fragrant alcohols to form alkoxy silanes (U.S. patents 4,524,018 and 4,500,725). None of these approaches teach or suggest that an olefinically substituted silane containing one or more fragrant substituent groups can be prepared or if prepared would be useful in the preparation of personal care compositions.
  • GB-A-2041964 discloses soap compositions and GB-A-2042890 discloses antiperspirant and/or deodorant compositions which contain as a fragrance imparting component at least one silicon compound having attached to silicon at least one group of the general formula - OR wherein R represents the residue remaining after removal of the hydroxyl group from an alcohol selected from cyclic and acylic monoterpene alcohols, essential aryl-substituted aliphatic alcohols and essential aliphatic-substituted phenols.
    • SUMMARY OF THE INVENTION
  • The present invention provides for a silicon compound having the formula:

            (R1O)a(R2O)b(R3O)c(R4)d(R5)eSiR6

    where R1, R2 and R3 are derived from the group of fragrant alcohols consisting of R1OH, R2OH and R3OH as defined in claim 1 with R4 and R5 selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms, R6 is a two to forty atom monovalent unsaturated hydrocarbon radical containing a terminal olefinic or acetylenic moiety where the subscript a has a value ranging from 1 to 2 and the subscripts b, c, d, and e have values ranging from 0 to 2 subject to the limitation that a + b + c + d + e = 3, and d or e is at least 1. The invention also relates to compositions containing the above silicon compounds.
    • DETAILED DESCRIPTION OF THE INVENTION
  • The compounds of the present invention introduce fragrant moieties into an olefinic silane molecule. The olefinic silane molecule is capable of further reaction under hydrosilylation conditions to form a variety of siloxanes that also possess fragrant moieties. These siloxane molecules are useful in a variety of personal care compositions. The present invention is directed to new compositions of matter that are silanes that release a fragrant alcohol, ester, ketone or aldehyde upon particular subsequent chemical reactions. Typically the subsequent chemical reaction that releases the fragrant alcohol is a hydrolysis reaction. Furthermore these silanes may be reacted to form siloxanes that release a fragrant alcohol upon the same particular subsequent chemical reactions wherein the olefinic silane precursor also releases a fragrant alcohol, ester, ketone or aldehyde.
  • The compounds of the present invention are described by the formula:

            (R1O)a(R2O)b(R3O)c(R4)d(R5)eSiR6

    where R1, R2 and R3 are selected (or derived from) from the group of alcohols consisting of R1OH, R2OH and R3OH wherein R1OH, R2OH and R3OH are fragrant alcohols as defined in claim 1, with R4 and R5 selected from the group consisting of monovalent hydrocarbon radical having from one to forty carbon atoms R6 a two to forty atom monovalent unsaturated hydrocarbon radical containing a terminal olefinic or acetylenic moiety where the subscript a has a value ranging from 1 to 2 and the subscripts b, c, d, and e have values ranging from 0 to 2 subject to the limitation that a + b + c + d + e = 3 and d or e is at least 1. As used herein, the phrase monovalent hydrocarbon radical includes both aliphatic and aromatic monovalent hydrocarbon radicals that may also include hetero-atoms such as oxygen, nitrogen, sulfur and the halogens, fluorine, chlorine, bromine and iodine.
  • The following synthetic examples are intended to illustrate the general synthetic reactions schemes that a person having ordinary skill in the art of silicones chemistry would typically employ in order to prepare the compounds of the present invention. These reaction schemes are thus illustrative only and do not represent the only synthetic pathways by which the compounds of the present invention may be prepared.
  • When the starting material is a fragrant alcohol such as phenethanol, olefinic halosilanes or olefinic silicon alkoxides may be employed as starting materials to produce the fragrance-releasing silanes of the present invention. Applicant herewith defines the phrase olefinic silicon alkoxide to be a monomeric silicon compound wherein a single silicon atom is substituted with four monovalent organic substituents one of which is an olefin and one of which is an alkoxide.
    Figure imgb0001
    Figure imgb0002
    Similarly 3-methyl-5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol will react with chloromethylvinylsilane in a similar fashion, reaction scheme IV:
    Figure imgb0003
    as will allyldimethylchlorosilane react with citronellol in a similar, reaction scheme V:
    Figure imgb0004
  • The fragrant alcohols that are precursors of the silanes of the present invention are selected from the group consisting of 3-methyl-5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methylbutanol, 3-pentanol, n-pentanol, 2-pentanol, n-hexanol, 2-methylpentanol, 1-decanol, sandela, nonadyl, dimetol, thymol, 1-heptanol, menthol, eugenol, vanillan, o-vanillan, 4-(p-hydroxyphenyl)-2-butanone, syringealdehyde, prenol, cis-3-hexenol, trans-3-hexenol, cis-4-heptenol, trans-2-octenol, trans-2-cis-6-nonadienol, geraniol, nerol, citronellol, crotyl alcohol, oleyl alcohol, linalool, α-terpineol, β-phenethyl alcohol, cinnamic alcohol, benzyl alcohol, α-methylbenzyl-alcohol, nonyl alcohol, 1-octanol, 3-octanol, phenethyl salicylate, hydrocinnayl alcohol, cis-6-nonen-1-ol, trans-2-nonen-1-ol, methyl salicylate, cis-3-octen-ol, anisyl alcohol, carvacrol, dihydrocarveol, benzyl salicylate, tetrahydrogeraniol, ethyl salicylate, ethyl vanillin, isoeugenol, isopulegol, lauryl alcohol, tetrahydrolinalool and 2-phenoxyethanol.
  • The fragrance releasing compounds of the present invention are particularly suited to incorporation into personal care products to impart a desirable long lasting fragrance to the products. Suitable uses include but are not limited to deodorants, antiperspirants, skin creams, facial creams, hair care products such as shampoos, mousses, styling gels, protective creams, shaving creams, after shave, cologne, perfume, color cosmetics such as lipsticks, foundations, blushes, makeup, and mascara; and other cosmetic formulations where other silicon containing components have been added and where it is desirable to impart a fragrance. Incorporation of small amounts of the compositions of the present invention into fragrance products such as shaving lotions, colognes, toilet water, and perfumes can impart a desirable long lasting fragrance to these products. Further, the silanes of the present invention may incorporated into other products where it is desirable to mask unpleasant odors with a pleasant fragrance for example household cleaning products such as waxes and polishes, automobile cleaning products such as waxes and polishes, detergents, textile coatings, paints, varnishes and the like subject to the limitation that the silane of the present invention be compatible or capable of being rendered compatible with the product in which it is incorporated.
    Experimental Preparation of Dimethylvinylphenethyloxysilane, Dimethylvinylchlorosilane (150 mL, 1.099 moles) was added to a stirred solution of phenethyl alcohol (124.5 mL, 1.042 moles), triethylamine (TEA, 155 mL, 1.112 moles) and toluene (300 mL) over 1.5 h. After addition, the reaction was heated to 65°C for 0.5 h then cooled to room temperature, filtered, the filter cake washed with toluene (200 mL), the filtrate concentrated in vacuo and then vacuum distilled (81-85°C/533 Pa (4 mm Hg)) to give product (180.5g, 84%).
    Bis(phenethyloxy)methylvinylsilane, - Dichloromethylvinylsilane (80g, 0.567 moles) was added to a stirred solution of phenethyl alcohol (140 g, 114 moles), triethylamine (TEA, 121 g, 1.2 moles) and Isopar C (700 mL) over one hour during which time the reaction mixture was heated to 70 °C. After an additional one hour, the reaction was cooled to room temperature, filtered, concentrated in vacuo and then stripped under high vacuum distilled (110°C at 533 Pa (4 mm Hg)) to give product (166 g, 94%).
    Dimethyl(3-methyl-5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-oxy)vinyisilane, - Dimethylchlorovinylsilane (10.0 mL, 0.073 moles) diluted with toluene (25 mL), was added to a stirred solution of 3-methyl-5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol (16.40 g, 0.077 moles), triethylamine (TEA, 7.8 g, 0.077 moles) and toluene (100 mL) over 20 min during. The mixture was then heated to 60 °C. After 6 hours, the reaction was cooled to room temperature, filtered, concentrated in vacuo and then stripped and distilled under high vacuum distilled (75-77°C/ 40 Pa (0.3 mm Hg)) to give product (166 g, 94%).

Claims (4)

  1. A silicon compound having the formula:

            (R1O)a(R2O)b(R3O)c(R4)d(R5)eSiR6

    where R1, R2 and R3 are derived from fragrant alcohols selected from the group consisting of 3-methyl-5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methylbutanol, 3-pentanol, n-pentanol, 2-pentanol, n-hexanol, 2-methylpentanol, 1-decanol, sandela, nonadyl, dimetol, thymol, 1-heptanol, menthol, eugenol, vanillan, o-vanillan, 4-(p-hydroxyphenyl)-2-butanone, syringealdehyde, prenol, cis-3-hexenol, trans-3-hexenol, cis-4-heptenol, trans-2-octenol, trans-2-cis-6-nonadienol, geraniol, nerol, citronellol, crotyl alcohol, oleyl alcohol, linalool, α-terpineol, β-phenethyl alcohol, cinnamic alcohol, benzyl alcohol, α-methylbenzyl alcohol, nonyl alcohol, 1-octanol, 3-octanol, phenethyl salicylate, hydrocinnayl alcohol, cis-6-nonen-1-ol, trans-2-nonen-1-ol, methyl salicylate, cis-3-octen-ol, anisyl alcohol, carvacrol, dihydrocarveol, benzyl salicylate, tetrahydrogeraniol, ethyl salicylate, ethyl vanillin, isoeugenol, isopulegol, lauryl alcohol, tetrahydrolinalool and 2-phenoxyethanol with R4 and R5 selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms, R6 is a two to forty atom monovalent unsaturated hydrocarbon radical containing a terminal olefinic or acetylenic moiety where the subscript a has a value ranging from 1 to 2 and the subscripts b, c, d, and e have values ranging from 0 to 2 subject to the limitation that a + b +c+d+e=3 and d or e is at least 1.
  2. A composition comprising a silicon compound of claim 1.
  3. The compound of claim 1 or composition of claim 2 wherein the subscript a has a value of 2.
  4. A cosmetic composition comprising the composition of claim 2.
EP99306790A 1998-08-28 1999-08-26 Fragrance releasing olefinic silanes Expired - Lifetime EP0982313B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US143136 1980-04-23
US09/143,136 US6046156A (en) 1998-08-28 1998-08-28 Fragrance releasing olefinic silanes

Publications (3)

Publication Number Publication Date
EP0982313A2 EP0982313A2 (en) 2000-03-01
EP0982313A3 EP0982313A3 (en) 2001-10-24
EP0982313B1 true EP0982313B1 (en) 2006-02-01

Family

ID=22502753

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99306790A Expired - Lifetime EP0982313B1 (en) 1998-08-28 1999-08-26 Fragrance releasing olefinic silanes

Country Status (4)

Country Link
US (2) US6046156A (en)
EP (1) EP0982313B1 (en)
JP (1) JP4562224B2 (en)
DE (1) DE69929659T2 (en)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6075111A (en) * 1998-08-28 2000-06-13 General Electric Company Fragrance releasing non-volatile polymeric siloxanes
US6054547A (en) * 1998-08-28 2000-04-25 General Electric Company Fragrance releasing non-volatile polymeric-siloxanes
US6949587B1 (en) * 1999-08-06 2005-09-27 Ecosmart Technologies, Inc. Pesticidal compositions containing plant essential oils against beetles
US20030203978A1 (en) * 2001-05-16 2003-10-30 O'brien Michael Joseph Cosmetic compositions comprising silicone gels comprising entrapped, occluded or encapsulated pigments
US6538061B2 (en) 2001-05-16 2003-03-25 General Electric Company Cosmetic compositions using polyether siloxane copolymer network compositions
US7241835B2 (en) * 2001-05-16 2007-07-10 General Electric Company Cosmetic compositions comprising silicone gels
US6531540B1 (en) 2001-05-16 2003-03-11 General Electric Company Polyether siloxane copolymer network compositions
US20030095935A1 (en) * 2001-11-16 2003-05-22 General Electric Company Transfer resistant cosmetic compositions comprising silicone gels
DE10338070A1 (en) * 2003-08-19 2005-03-17 Henkel Kgaa Agent on substrate surfaces
US20050164063A1 (en) * 2003-10-20 2005-07-28 Fuji Photo Film Co., Ltd. Compound, and solid electrolyte, proton conductor, membrane electrode assembly and fuel cell comprising the compound
US7579495B2 (en) * 2003-12-19 2009-08-25 Momentive Performance Materials Inc. Active-releasing cyclic siloxanes
US7576170B2 (en) * 2003-12-19 2009-08-18 Momentive Performance Materials Cyclic siloxane compositions for the release of active ingredients
US7935842B2 (en) 2006-02-09 2011-05-03 Momentive Performance Materials Inc. Hydrolysis resistant organomodified trisiloxane surfactants
US20070197394A1 (en) * 2006-02-17 2007-08-23 General Electric Company Hydrolysis resistant organomodified trisiloxane surfactants
US20070249560A1 (en) 2006-04-21 2007-10-25 Leatherman Mark D Hydrolysis resistant organomodified silyated surfactants
US20080033136A1 (en) * 2006-07-13 2008-02-07 Rinard Chauncey J Selective hydrosilylation conditions
US7259220B1 (en) * 2006-07-13 2007-08-21 General Electric Company Selective hydrosilylation method
US7964032B2 (en) * 2006-10-17 2011-06-21 Momentive Performance Materials Inc. Fluorine-free trisiloxane surfactant compositions for use in coatings and printing ink compositions
US7399350B2 (en) * 2006-10-17 2008-07-15 Momentive Performance Materials Inc. Fluorine-free disiloxane surfactant compositions for use in coatings and printing ink compositions
US7879916B2 (en) * 2006-12-11 2011-02-01 Momentive Performance Materials Inc. Hydrolysis resistant organomodified silylated ionic surfactants
US20080167269A1 (en) * 2006-12-11 2008-07-10 Momentive Performance Materials Inc. Hydrolysis resistant organomodified silylated ionic surfactants
BRPI0721421A2 (en) 2007-03-08 2013-01-01 Momentive Performance Mat Inc hydrolysis resistant organomodified trisiloxane surfactants
BRPI0721410A2 (en) 2007-03-08 2013-01-01 Momentive Performance Mat Inc hydrolysis resistant organomodified trisiloxane surfactants
WO2009061362A2 (en) 2007-11-02 2009-05-14 Momentive Performance Materials Inc. Textiles treated with copolymers of epoxy compounds and amind silanes
US20090173913A1 (en) * 2007-12-26 2009-07-09 Momentive Performance Materials Inc. Hydrolysis resistant organomodified disiloxane ionic surfactants
US20090176893A1 (en) * 2007-12-26 2009-07-09 Momentive Performance Materials Inc. Hydrolysis resistant organomodified trisiloxane ionic surfactants
US20090171108A1 (en) * 2007-12-26 2009-07-02 Momentive Performance Materials Inc. Mixtures comprising hydrolysis resistant organomodified disiloxane ionic surfactants
US20090173912A1 (en) * 2007-12-26 2009-07-09 Momentive Performance Materials Inc. Mixtures of hydrolysis resistant organomodified trisiloxane ionic surfactants
JP5133092B2 (en) * 2008-03-06 2013-01-30 花王株式会社 Functional substance release agent
CN102438583A (en) * 2008-12-18 2012-05-02 莫门蒂夫性能材料股份有限公司 Composition comprising at least two different cycloalkylmethicones and use thereof
WO2011079187A1 (en) 2009-12-23 2011-06-30 Momentive Performance Materials Inc. Network copolymer crosslinked compositions and products comprising the same
EP2601245A1 (en) 2010-08-05 2013-06-12 Biofilm IP, LLC Cyclosiloxane-substituted polysiloxane compounds, compositions containing the compounds and methods of use thereof
JP5253608B2 (en) * 2011-07-26 2013-07-31 花王株式会社 Perfume release agent
US8497338B2 (en) 2011-10-31 2013-07-30 Momentive Performance Materials Inc. Process of manufacturing organosilicon products with improved quality using heterogeneous precious metal catalysts
EP3122429B1 (en) 2014-03-26 2018-05-09 Momentive Performance Materials Inc. Silylated surfactants in personal care and home care
CN107108897A (en) * 2014-11-14 2017-08-29 宝洁公司 Organo-silicon compound
US20160186073A1 (en) * 2014-12-30 2016-06-30 Shell Oil Company Methods and systems for processing cellulosic biomass
US20160184734A1 (en) * 2014-12-30 2016-06-30 Shell Oil Company Methods and systems for processing cellulosic biomass
US20160186066A1 (en) * 2014-12-30 2016-06-30 Shell Oil Company Methods and systems for processing cellulosic biomass
US20160186068A1 (en) * 2014-12-30 2016-06-30 Shell Oil Company Methods and systems for processing cellulosic biomass
CN104672268A (en) * 2015-03-06 2015-06-03 苏州阳桥化工科技有限公司 Preparation method of dimethyl bis(banzyloxy) silane compound serving as flame retardant
US9988404B2 (en) 2016-04-07 2018-06-05 Momentive Performance Materials Inc. Ester-modified organosilicon-based surfactants, methods of making same and applications containing the same
EP3269723A1 (en) * 2016-07-13 2018-01-17 Nitrochemie Aschau GmbH Hardener for silicone rubber masses
US10442821B2 (en) 2016-08-01 2019-10-15 Takasago International Corporation Method for releasing unsaturated aldehyde or ketone
JP7544730B2 (en) 2019-03-08 2024-09-03 ザ プロクター アンド ギャンブル カンパニー Compositions containing siloxane compounds having pendant silyl ether moieties

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2679496A (en) * 1954-05-25 Production of organosilicon
US3271305A (en) * 1961-09-01 1966-09-06 Dan River Mills Inc Textile treatments and treated textiles
US3215719A (en) * 1961-09-01 1965-11-02 Dan River Mills Inc Silicate esters of essential alcohols
NL128386C (en) * 1964-10-12
FR1439013A (en) * 1964-10-28 1966-05-20 Rhone Poulenc Sa Process for the preparation of 1-alkene yloxysilanes and analogous compounds
US3779987A (en) * 1972-10-12 1973-12-18 Gen Electric Process for producing diorganopolysiloxane polymers
DE2519720A1 (en) * 1975-05-02 1976-11-11 Dynamit Nobel Ag Unsaturated ORGANIC SILICONE COMPOUNDS CONTAINING KETO GROUPS
IT1209302B (en) * 1979-02-01 1989-07-16 Dow Corning Ltd SOAP-BASING COMPOSITION CONTAINING SILICON COMPOUNDS SUCH AS LONG-LAST PERFUMED INGREDIENTS
NL8000387A (en) * 1979-02-01 1980-08-05 Dow Corning PREPARATION WITH ANTI-TRANSPIRATION AND / OR DEODORANT PROPERTIES.
US5157120A (en) * 1980-09-16 1992-10-20 Syntex (U.S.A.) Inc. Guanine derivatives
US4332957A (en) * 1980-12-22 1982-06-01 National Distillers & Chemical Corp. Phenoxyalkoxy silanes
JPS5822063A (en) * 1981-07-30 1983-02-09 チッソ株式会社 Aromatic agent
US4500725A (en) * 1981-07-30 1985-02-19 Chisso Corporation Silane derivative and fragrant article
US4445641A (en) * 1982-01-08 1984-05-01 Bend Research, Inc. Controlled-release dispenser
JPS58208211A (en) * 1982-05-28 1983-12-03 Chisso Corp Aromatic agent prepared by using slowly decomposable perfume
US4613680A (en) * 1982-06-28 1986-09-23 Toray Industries, Inc. Preparation of angelic acid or esters thereof
DE3230867A1 (en) * 1982-08-19 1984-02-23 Bayer Ag, 5090 Leverkusen OLEFINICALLY UNSATURATED SILOXANES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A REACTIVE THINNER FOR RADICALLY CROSSLINKABLE LACQUER SYSTEMS
JPS59155451A (en) * 1983-02-22 1984-09-04 Asahi Glass Co Ltd Perfume-containing resin
US4880851A (en) * 1987-02-26 1989-11-14 Tohru Yamamoto Aromatic composition and method for the production of the same
US5008115A (en) * 1988-04-22 1991-04-16 Dow Corning Corporation Matrix for release of active ingredients
US4908208A (en) * 1988-04-22 1990-03-13 Dow Corning Corporation Matrix for release of active ingredients
FR2643572A1 (en) * 1988-12-22 1990-08-31 Rhone Poulenc Chimie METHOD FOR ENCAPSULATING PARTICLES BY FILMING USING A THERMOPLASTIC SILICONE COPOLYMER
US5110971A (en) * 1989-07-05 1992-05-05 Aristech Chemical Corporation Silyl derivatives of eugenol
US5266663A (en) * 1989-07-05 1993-11-30 Aristech Chemical Corporation Silyl derivatives of eugenol
US5071704A (en) * 1990-06-13 1991-12-10 Fischel Ghodsian Fariba Device for controlled release of vapors and scents
GB9021061D0 (en) * 1990-09-27 1990-11-07 Unilever Plc Encapsulating method and products containing encapsulated material
US5387411A (en) * 1990-10-05 1995-02-07 Dow Corning Corporation Antiperspirant containing a hydrophobic macroporous polymer as the suspending agent
US5234689A (en) * 1990-11-08 1993-08-10 La Parfumerie, Inc. Multi-purpose fragrance composition
US5176903A (en) * 1990-12-13 1993-01-05 Revlon Consumer Products Corporation Antiperspirant/deodorant containing microcapsules
CA2124789C (en) * 1991-12-20 1998-07-28 Gregory Berry A process for preparing a perfume capsule composition
US5372806A (en) * 1992-01-03 1994-12-13 Soft And Shine Grooming composition
US5160494A (en) * 1992-04-14 1992-11-03 Dow Corning Corporation Alkylmethylsiloxane containing perfume compositions
US5508259A (en) * 1993-02-11 1996-04-16 Firmenich Sa Perfuming composition
JP3304219B2 (en) * 1993-11-11 2002-07-22 カネボウ株式会社 Sustained release fragrance composition for human body surface
US5424018A (en) * 1994-01-13 1995-06-13 General Electric Company Variable width die and method for extruding sheet products
US5447893A (en) * 1994-08-01 1995-09-05 Dow Corning Corporation Preparation of high density titanium carbide ceramics with preceramic polymer binders
US5525588A (en) * 1994-09-14 1996-06-11 Elzabeth Arden Co. Cosmetic composition
US5449512A (en) * 1994-08-24 1995-09-12 The Procter & Gamble Company Anhydrous after shave lotions
US5490982A (en) * 1995-02-01 1996-02-13 Elizabeth Arden Company, Division Of Conopco, Inc. Cosmetic composition
CH689622A5 (en) * 1995-03-15 1999-07-15 Firmenich & Cie Polysiloxane new, their use in perfumery and process for their preparation.
JPH08310930A (en) * 1995-05-15 1996-11-26 Lion Corp Composition for oral cavity
CA2249281C (en) * 1996-03-19 2005-07-12 The Procter & Gamble Company Built automatic dishwashing compositions comprising blooming perfume
JPH10237175A (en) * 1996-11-22 1998-09-08 General Electric Co <Ge> Fragrance-releasing nonvolatile polymerlike siloxane
EP0878497A3 (en) * 1997-05-15 1999-12-15 Givaudan-Roure (International) S.A. Fragrance precursor compounds
US6054547A (en) * 1998-08-28 2000-04-25 General Electric Company Fragrance releasing non-volatile polymeric-siloxanes
US6083901A (en) * 1998-08-28 2000-07-04 General Electric Company Emulsions of fragrance releasing silicon compounds
US6075111A (en) * 1998-08-28 2000-06-13 General Electric Company Fragrance releasing non-volatile polymeric siloxanes

Also Published As

Publication number Publication date
DE69929659D1 (en) 2006-04-13
JP4562224B2 (en) 2010-10-13
US6046156A (en) 2000-04-04
DE69929659T2 (en) 2006-12-07
JP2000109489A (en) 2000-04-18
US6153578A (en) 2000-11-28
EP0982313A3 (en) 2001-10-24
EP0982313A2 (en) 2000-03-01

Similar Documents

Publication Publication Date Title
EP0982313B1 (en) Fragrance releasing olefinic silanes
EP0982022B1 (en) Fragrance releasing non-volatile polymeric siloxanes
EP0998911B1 (en) Fragrance releasing non-volatile polymeric siloxanes
JPH10237175A (en) Fragrance-releasing nonvolatile polymerlike siloxane
JP2000119394A5 (en)
EP1697386B1 (en) Active ingredient-releasing cyclic siloxanes
JP2527093B2 (en) Organic silicon compounds and cosmetics
JP2022515662A (en) Acrylate-functional branched organosilicon compounds, methods for preparing them, and copolymers formed thereby.
EP1716159B1 (en) Bicyclic siloxane compositions for the release of active ingredients
JP4084514B2 (en) New indanilidene compounds
WO2005000856A2 (en) Siloxane compounds
JP2720127B2 (en) Fluorine-modified silicone, process for producing the same, and cosmetic containing the same
JP3425508B2 (en) Novel organosilicon compounds and cosmetics containing the same
JPH1072394A (en) Perfluoroalkyl compound

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

Kind code of ref document: A2

Designated state(s): DE FR GB

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

RIC1 Information provided on ipc code assigned before grant

Free format text: 7C 07F 7/18 A, 7A 61K 7/00 B, 7A 61K 7/46 B

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE

AX Request for extension of the european patent

Free format text: AL;LT;LV;MK;RO;SI

17P Request for examination filed

Effective date: 20020424

AKX Designation fees paid

Free format text: DE FR GB

17Q First examination report despatched

Effective date: 20030310

GRAP Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOSNIGR1

GRAS Grant fee paid

Free format text: ORIGINAL CODE: EPIDOSNIGR3

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

RIC1 Information provided on ipc code assigned before grant

Ipc: A61K 8/58 00000000ALI20051205BHEP

Ipc: A61K 8/00 00000000ALI20051205BHEP

Ipc: C07F 7/18 19680901AFI20051205BHEP

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE FR GB

REG Reference to a national code

Ref country code: GB

Ref legal event code: FG4D

REF Corresponds to:

Ref document number: 69929659

Country of ref document: DE

Date of ref document: 20060413

Kind code of ref document: P

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed

Effective date: 20061103

REG Reference to a national code

Ref country code: DE

Ref legal event code: R082

Ref document number: 69929659

Country of ref document: DE

Representative=s name: MAI DOERR BESIER PATENTANWAELTE, DE

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20130828

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20130827

Year of fee payment: 15

Ref country code: FR

Payment date: 20130819

Year of fee payment: 15

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 69929659

Country of ref document: DE

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20140826

REG Reference to a national code

Ref country code: DE

Ref legal event code: R119

Ref document number: 69929659

Country of ref document: DE

Effective date: 20150303

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

Effective date: 20150430

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20150303

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20140826

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20140901